Hydrogen Bromide → HCID 58589656, compound

HRID 1953838Notes

Reaction equation

HRID 1953838 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.O.[BrH:16].[Br:17]Br>C([O-])(C)(C)C.N1C=CC=CC=1>[Br:16][C:10]1([Br:17])[C:9]2[C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3][C:2]1=[O:1]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 24408BromineHCID 18671947Methyl 2-oxo-2,3-dihydro-1H-indole-4-carboxylate

Product 1

HCID 58589656HCID 58589656, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 45749132-Methylpropan-2-olateSolvent

Procedure

2,3-Dihydro-2-oxo-1H-indole-4-carboxylic acid, methyl ester, (C. A. Grob and 0. Weissbach, Hely. Chim. Acta, vol. 44, p. 1736, 1961) (2 g, 11.4 mmol) was dissolved in t-butylhydroxide (120 mL) containing 0.5 mL of water. Pyridine.hydrogen bromide.bromine (14.6 g, 45.7 mmol) was added and the mixture was stirred at room temperature for 16 hours. The reaction was quenched by the addition of water and the t-butylhydroxide was distilled off. The resulting residue was partitioned between water and ethyl acetate, and the ethyl acetate was dried with magnesium sulfate, filtered and concentrated in vacuo to yield the title compound (3.92 g, 98%).

Workup

  1. customThe reaction was quenched by the addition of water
  2. distillationthe t-butylhydroxide was distilled off
  3. customThe resulting residue was partitioned between water and ethyl acetate
  4. dry with materialthe ethyl acetate was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf4c26377a9e45e1bbeaea5cf51677bd
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

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